In 2018, when I ran for office in Chicago, I worked with Bobby Moesta and the ReWired Group to figure out something nobody on the campaign trail seemed to want to ask honestly: why is Chicago one of the only major American cities losing population?

The standard answers are the policy ones. Taxes. Crime. Schools. Pension obligations. Each of those gets you a chart and a talking point. None of them gets you the truth.

So we used Jobs to be Done. Bobby's framework. Dozens of forensic interviews with people who had recently moved to or away from the city. The point was simple. Stop asking "why did you leave Chicago" and start asking "tell me the story of how you ended up where you are now." When people tell stories, they tell you what actually moved them.

Four patterns came out of those conversations. The two that mattered most for our campaign were the leaving ones.

A mom I talked to had twin boys in their first year of Catholic school. In December, the school told her they couldn't grade her sons because they couldn't read. The school had no resources for dyslexia. The family moved to the suburbs. The decision hinged on one thing: where will our kids get the best shot at learning to read. Nothing else mattered. Another family's local police station closed. Neighbors had a window shot out while their kids were sleeping. She organized CAPS meetings. Nobody came when she called the police. They moved out too.

A finance guy and his wife, a doctor, had three kids under five, a small condo in the South Loop, no yard, no family within a thousand miles. They moved to Cleveland because his family was there and a house with a yard was a fantasy in Chicago. A recent Northwestern engineering grad got low-balled by Chicago employers, visited a friend in Louisville, saw a nice apartment for half the rent, and took a job there. He wanted to come back. He couldn't make the math work yet.

The other two patterns were people moving to Chicago for community and culture, and people passing through for the experience of somewhere new. We set the experience-seekers aside. They weren't going to be persuaded by any campaign. They were already gone.

What struck me reading the transcripts back then, and it strikes me harder now, is that nobody talked about a tax rate. And nobody recited a crime statistic. They told us the moment. The week their kid couldn't be graded, the night the neighbors' window got shot out, the day they realized their family of five could afford a yard somewhere else but never here.

The lesson comes when you stop asking what your product or your city (or your campaign) is doing. And you start asking what's actually happening in the life of the person making the choice. You let them tell you the story of the moment they decided, and you trust the story over the chart.

It works for companies. It works for cities. It works for everything else too (even relationships). The same lens explains why someone switches from Notion to Linear, why a parent picks a school, why a patient drives past three hospitals to see one specific doctor. Most of us keep tuning the thing we're offering. The person making the choice is over here, holding the moment that finally pushed them one way or the other.

From 2023 to 2025 I split my time between Chicago and the Bay Area, teaching at Northwestern while living part of the year in Oakland and San Francisco. Both cities were going through their own version of this. The headlines were tech exodus, downtown vacancy, recalls, retail theft, the doom loop. The stories underneath were the same shape as Chicago's. Someone whose street tipped in a direction they couldn't accept. Someone whose company offered remote and a friend in Austin had an extra bedroom. Someone whose kid was about to start kindergarten and family was somewhere else. The official explanations changed city to city. The actual stories rhymed.

I keep coming back to this work. Chicago is still one of the only major U.S. cities losing vital sub-populations. The conversation about why is still mostly about the things you can put on a chart. Property taxes too high. Schools underfunded. Police under-resourced. All partly true. None of them are the reason that mom moved to the suburbs. If we figured out Chicago's puzzle honestly, I think we'd be holding the key for a lot of American cities. The rankings differ. The stories rhyme.

I wrote a piece a few weeks ago about Chicago's teen takeovers that landed on the same instinct, pointed at a different question. The organizing capacity isn't the problem. It might be the most underutilized asset we have. Stop telling our kids what they're doing wrong. Start asking what they're actually trying to do.

(And for what it's worth, this is also most of what we do at Shokuna these days, the research practice I run with Lilliana Robinson. Our battle-tested playbook pointed at whatever someone is trying to build. Mentioning it because people ask.)

I'm still thinking about Chicago, and other cities in a similar situation. About what it would take to get those families to come home, and be better off having done so. About the kinds of campaigns that would actually ask the question instead of polling around it and yelling at clouds.

If you want to know why someone left, don't ask them why. Ask them when.